Hydrazine hydrate (1:1) → HCID 45496782, compound

HRID 870857Notes

Reaction equation

HRID 870857 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:14]1([C:19](N2C=CN=C2)=[S:20])C=CN=C1.O.[NH2:27]N>C1COCC1>[NH:14]([C:19]([N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)=[S:20])[NH2:27]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 802641,1'-ThiocarbonyldiimidazoleHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 45496782HCID 45496782, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TEA (2.1 mL, 0.015 mol) was added to a solution of tert-butyl piperazine-1-carboxylate (1.86 g, 0.01 mol) and di-(1H-imidazol-1-yl)methanethione (2.67 g, 0.015 mol) in THF (30 mL) at rt. The reaction mixture was stirred at rt for 2 hrs., then hydrazine hydrate (0.73 mL, 0.015 mol) was added. The resultant solution was stirred at rt for another 2 hrs. The reaction mixture was quenched with saturated sodium chloride (15 mL) and extracted with EtOAc (3×). The combined organic layer was dried over Na2SO4, concentrated and recrystallized (3:1 petroleum ether/EtOAc) to afford tert-butyl 4-(hydrazinecarbonothioyl)piperazine-1-carboxylate (2.2 g, 85%) as a light yellow solid.

Workup

  1. customThe reaction mixture was quenched with saturated sodium chloride (15 mL)
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customrecrystallized (3:1 petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-689f23bfb9504114a70f8f71af9d29b5
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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